Lutein - Compound Card

Lutein

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Lutein

Structure
Zoomed Structure
  • Family: Protista - Haematococcaceae
  • Kingdom: Plantae, Protista
  • Class: Terpenoid
    • Subclass: Carotenoid
Canonical Smiles C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C)\C
InChI InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1
InChIKey KBPHJBAIARWVSC-RGZFRNHPSA-N
Formula C40H56O2
HBA 2
HBD 2
MW 568.89
Rotatable Bonds 10
TPSA 40.46
LogP 10.4
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 568.43
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Uvaria lucida ssp. lucida Annonaceae Plantae 509419
2 Vernonia urticifolia Asteraceae Plantae 3032568
3 Vernonia urticifolia Asteraceae Plantae 3032568
4 Leucas martinicensis Lamiaceae Plantae 483832
5 Vernonia urticifolia Rutaceae Plantae 3032568
6 Haematococcus pluvialis Haematococcaceae Protista 44745

Showing of synonyms

  • Ele S, G/Yesus T, et al. (2007). Chemical studies of Leucas martinicensis. M.Sc. Thesis, Addis Ababa University, Ethiopia,2007. [View] [PubMed]
  • El-Baz F.K, Hussein R.A, et al. (2018). Cytotoxic activity of carotenoid rich fractions from Haematococcus pluvialis and Dunaliella salina microalgae and the identification of the phytoconstituents using LC‐DAD/ESI‐MS.. Phytotherapy research : PTR, 2018, 32(2), 298-304. [View] [PubMed]
  • Kiplimo JJ, Everia CA, et al. (2011). Novel polyene from Vernonia urticifolia (Asteraceae). Journal of Medicinal Plants Research,2011,5(17),4202-4211. [View] [PubMed]
  • Achenbach H, Höhn M, et al. (1997). Oxygenated pyrenes, their potential biosynthetic precursor and benzylated dihydroflavones from two African Uvaria species. Phytochemistry,1997,44(29),359-364. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
Pubchem: 5281243
Kegg Ligand: C08601
Chebi: 28838
Nmrshiftdb2: 60020146
Metabolights: MTBLC28838
Drugbank: DB00137
CPRiL: 61011
Structure

SMILES: C1CCCC=C1C=CC=CC=CC=CC=CC=CC=CC=CC=CC2C=CCCC2

Level: 1

Mol. Weight: 568.89 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 568.89 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.05
Plasma Protein Binding
98.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-1.43
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.59
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.87
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.28
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-2631.63
Rat (Acute)
3.1
Rat (Chronic Oral)
2.64
Fathead Minnow
17.33
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
472.5
Hydration Free Energy
-3.09
Log(D) at pH=7.4
6.41
Log(P)
10.46
Log S
-7.03
Log(Vapor Pressure)
-7.6
Melting Point
195.49
pKa Acid
15.22
pKa Basic
4.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.9606
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.9606
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9251
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9251
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9100
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9100
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9022
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9022
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9000
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9000
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8966
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8966
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8830
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8830
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8660
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8660
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8588
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8588
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8575
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8575
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8521
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8521
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8424
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8424
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8396
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8396
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8267
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8267
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8215
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8215
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8141
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8141
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8003
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8003
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7987
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7987
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7895
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7895
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7866
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7866
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7795
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7795
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7742
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7742
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7702
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7702
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7682
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7682
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7560
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7560
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7500
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7500
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7478
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7478
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7476
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7476
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7457
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7457
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7417
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7417
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7375
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7375
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7333
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7333
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7323
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7323
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7256
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7256
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7240
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7240
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7165
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7165
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7156
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7156
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7155
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7155
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7151
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7151
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7145
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7145
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7138
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7138
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7117
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7117
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7090
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7090
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7059
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7059
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7030
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7030
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7026
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7026
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7025
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7025
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7017
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7017
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7005
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7005

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